Week with Castiel
by darkestwinternight
Summary: Dean is a male escort, he has been called and paid for by a high paying ViP member Castiel Novak. Not much is said on the paper work Dean is given. But when Dean sees him he doesn't know wheather he entered heaven or hell.
1. Chapter 1

Dean collected his thoughts as he drove down the long winding driveway of his new clients home. There was not a lot to go on when he took a look at his file except a name Castiel Novak. He was one of the VIP members he pays well towards the company. Dean was told not to pack much as outfits and other essentials were to be provided for as long as he stayed. As Dean neared the house he noticed that the place was huge just stepping up each step he felt more and more out of place. He quickly snapped out of those dark thoughts and started into work mode and reached for the door bell, but before he could the door opened.

A tall skinny man with short black hair opened the door

"Yes," he sneered as he looked Dean up and down

"D-Dean Winchester for Castiel Novak," Dean started to stutter

"Yes, Dean Winchester, my apologizes please come in"

Dean entered the house and immediately was amazed by the fancy decor. The butler took Deans bags and brought them into the house.

"I shall call Mr. Novak, Please sit down"

"Name's Gordon by the way"

Gordon walked over towards an intercom and punched in a code and pushed enter

"WHAT', A loud voice screeched out of the intercom"SPEAK BEFORE I GET AGRIER FOR YOU INTERUPTING ME" He hissed

Gordon sighed " Dean Winchester the man you hired is here"

there was silence then Gordon went over to pick up Deans bag and said I will put this in your room which will be all the way in the back on the second floor to the right.

Dean moved right out of the way to let Gordon pass. He heard a CLICK from upstairs and a door opening, Dean stood straight up and tried to make himself look more presentable. When Dean looked up he could not believe his eyes a young man maybe a few years younger than him with Sandy hair Blue eyes, He could not stop looking at those blue eyes of his. He was was wearing a Black suit with a white shirt with a nice pressed black tie.

"I am Castiel Novak" he stonily says looking at dean then turning towards his backside "You may call me Cas or Sir"

"Ni-

"NO" He yelled, "you talk when I tell you to talk,you move when I tell you to move, you don't look at me unless I tell you. If I did not tell you to do it then you don't do it Agreed!?"

"Agree"

Castiel Smacked Dean and told him "what did I just finish telling you?"

He then sighed as he saw the print on Deans face, "Ugh, I guess I lost my temper, Go, GO to your room" Castiel had his hands on the bridge of his nose while he said that.

Dean made his way upstairs fighting back the tears he wanted to let fall. He entered the room and found the mirror looking at the hand print that was left on his face, It burned with pain and Dean put a cold towel on it to get the swelling to go down. What the hell has he gotten himself into.

Dean looked around the room, he even thought about taking a nap but was to afraid as to get in trouble if Cas needed him and he didn't answer. So he took a shower instead it felt great, he loved the water pressure and he felt like he could live there forever. He took some fancy shampoo and washed his hair still trying to forget the events that happened earlier. Half an hour went by and Dean got out of the shower when he noticed that there were outfits on his bed along with a note.

"Mr. Novak would like you to wear one of these

outfits for dinner. Oh and please call if you need anything

on the intercom right near your bed,

-Anna the maid

the intercom had a sheet next to it each with different room numbers with codes next to them. Dean wondered what the outfits had been picked out for him looked like, so he uncovered the wrapping on each one. He could not believe his eyes, the outfits were... not even considered outfits. Most of them were only half shirts and short shorts or just shorts. Guess he wants me to show off Dean chuckled to himself.

The intercom went off with a beep. "Dinner is Ready" a voice rang

Dean made his way down to the dining room to where the table was completely empty. Gordon motioned Dean to sit down and told him that Castiel would be soon joining him. He left Dean sitting in a big room by himself the silence was deafening he swore he could hear his heart beat.

Castiel walked in and Dean looked down as from earlier he was told not to look at him without consent first,

"You can look at me Dean" Cas said not looking up

He sat down and basically ignored Dean like he was not even there. Thank god the food got there quickly because it was becoming awkward and he was becoming anxious. The food was Delicious he was not used to this type of luxury

after he was done eating he was waiting for the command to go but for some reason Cas didn't look up from a newspaper he was reading, It must have been 30 or 40 minutes before Cas even said anything.

"Go into the living room and wait for me" he said not looking up

Dean was confused and just stared at him

"DID I FUCKEN STUTTER" he yelled.

Dean Jumped up at those words and power walked toward the living room. Dean entered the room and just stood in the middle because he didn't know whether it was OK for him to sit down. Cas came into the room with his hands folded behind his back.

"Strip" he said looking straight at Dean

Dean complied and started taking off his clothes, First his shirt, pants then his underwear. He was now standing completely naked in front of Cas. Cas started turning around him looking up and down but not saying anything. Cas went over to a drawer and took something long out of it but Dean could not make out what it was.

"Get down on your hands and Knees" He said coming back

Dean now knew what type of client Cas was and what he had gotten into. He has never experienced this type of Sexual play before so this is something new he was going to experience. He was just scared it was by this way.

Dean got down on his hands and knees and Cas got behind him which made Dean shudder with anticipation. Cas then laid his hands firmly on Deans ass and Gripped tight. The tightness of Casses hands made Dean jump. Then cas took his hands off Dean and a whipping pain came onto his left cheek. Two more came one after another and a new feeling came to Dean, He became half Erect at each whip he received.

"Getting Excited Dean" Cas Laughed

Dean was fully erect as the whips became more and more intense he was dripping with sweat and didn't know how much longer he could hold himself from collapsing onto the floor, More and more whips came and Dean noticed he was starting to ooze precum he was really enjoying himself he didn't know how long he was going to last before he explodes.

"You are not allowed to cum" Cas Hissed, "you Cum when I tell you to.

Dean is trying to hold it in, but it is proving very very difficult. Cas keeps whipping him in the way that makes it hard to concentrate on anything. Then all the sudden Cas stops. He walks towards the drawer and puts his toy away and the walks away into the next room.

What just happened Dean thought, he was still on his hands and knees not sure if he could get up or not. His hands were getting tired and his knees were hurting it must have been an hour he has been just staying in the same position. The door opened and Dean looked around him Cas looked at him and sighed.

"Oh I forgot you were still here, You may go to your room we are done for today"

Dean got up, got dressed and headed back toward his room

"What do we say?" Cas says not looking up from a book

Lost for words Dean realized what Cas wanted

"Th-Thank you sir" Dean said looking down

He then walked back to his room to take a shower and then get some well deserved sleep.  
:


	2. Chapter 2

Dean awoke to birds singing outside his window. He sat up and Stretched yawning while he did so. The morning was so beautiful he almost didn't want to leave his room to have breakfast, He slowly opened his door and it was very quiet no sounds at all. He saw a few maids go by but none talked to him nor even looked at him. He walked downstairs towards the dining room where Gordon was waiting at the bottom of the stairs for him.

"Good Morning Dean." he said with a bright smile

"Uh, Good morning to you too Gorgon" he said puzzled " Why are you at the bottom of the stairs"

" Making sure that you have your breakfast and to give you your list of things Mr. Novak would like to make sure you are aware of."

"He's not here?" Dean said with an eyebrow raised.

"No Dean, Mr. Novak has business meetings till noon"

Dean followed Gordon to the dining room where a waffle breakfast and fruit salad were waiting for him. Dean enjoyed every bite, he looked at the list that Cas left him and it told him that he was free to look around the house except for a few rooms (his room or the study) He was not allowed to make phone calls outside the house without consent from him directly. Treat the house just like if you lived here and enjoy your stay.

Dean finished up his breakfast and left the table and decided to go into the Garden area. He loved Flowers for some reason they gave him the sense of peace. He saw roses as he approached the area and immediately smelt them along with Jasmine and Lilacs. He didn't know how long he didn't know how long he was in there because he heard yelling after awhile. Dean walked into the living room to see Cas on the phone red in the face cursing up a storm. He backed away slowly to not draw attention to himself but Cas saw him and motioned for him to stay put.

"Crap" Dean said under his breath

he was afraid he was gonna get yelled at for walking into a conversation. Cas hung up his cell phone and walked over to Dean.

"Go downstairs, through the door on the left and stay there, I will be in shortly" He motioned his finger towards the basement door. His voice calm but still early enough that if Dean didn't go it could be Angry.

Dean followed the steps to the basement door, went to the left side door and entered. It was pitch black he couldn't see a thing, he tried to find a light switch by moving his fingers along the walls but no luck.

The door opened ten minutes later and the bright light from the door opening burned Deans eyes. The lights Flicked on with a clicker in Cas's hands.

"give me your hands" Cas said holding up chain link handcuffs.

Dean gave him his hands and Cas locked his hands into each of the cuffs

"Now your feet" Cas said holding Feet Cuffs

Dean gave him his feet no questions asked. He could not move his feet which made him anxious.

Cas bent down and hooked up a chain rope connecting a cuff to each of his feet to the floor. The same with the ones with his cuffs on his hands

"Good boy Dean." Cas said with a smirk

Cas then walked up to him and started undoing buttons on Deans shirt. His face was inches away from Deans face, He then trailed his pointer finger along Deans abs slowly which made Dean shudder with excitement. Cas's fingers trailed down lower and lower till the found the top of Deans shorts. Which by then Cas started to Unbuckle the belt. But then Cas stopped and walked over toward where the chains met and he pulled a lever. Each chain then moved and he then was splayed out. Cas then came back and finished unbuckling Deans belt. Dean could not move at all and that scared him but also gave him a thrill especially since every time Cas touched him he felt electricity. Before he knew it his underwear was being taken off, and he was exposed again.

Cas started stoking Deans Cock, slow and steadily.

Dean let out a small moan and that made Cas smirk

"Feels good I see," Cas said with sarcasm

Dean couldn't respond Cas was stroking him in the right spots that made him speechless. He was fully Erect that is when Cas stopped and walked away towards a wall full of his toys. Dean was confused on why Cas started out like this Today than like he did yesterday. But he chose not to judge today, Cas came back with a box full of things.

"Lets get started now that you're warmed up" Cas said with a wide smile

Cas pulled out a leather whip and smiled right at Dean as he did so. He then turned to Deans backed and whipped him across the shoulder blades. Dean cried out in pain

"SHUT UP" Cas yelled as he hit Dean again in the same spot

this time Dean kept his mouth shut and a single tear rolled down his cheek. But other than that nothing a few more whips on Deans back and then Cas was done. Cas moved toward Deans Face.

"Every time you make a noise I don't like I am going to discipline you" Cas said sternly.

Dean Nodded in agreement not making eye contact with Cas.

"Now, Lets see how far you can go" Cas smirks again

Cas pulls out a butt-plug and goes up to Dean again.

"Don't worry, I am not just gonna shove this up you" He laughs

Cas puts his hands on Deans ass hard and starts massaging each cheek, then starts to spread them apart till Dean can feel Cas's finger just over his hole. Then without warning Cas sticks a finger deep into him, Then pulls out and then sticks it back in. He starts slowly fingering Dean with one finger than two, three and before he knows it cas's whole fist is in Deans ass. Cas then takes his hand out and wipes his hand on a towel he gets the butt-plug and shoves it hard up Dean that cries out in pleasure. This time Dean is dripping with precum from the fisting he just got.

"Good Boy" Cas smiles "you Deserve an award.

Cas bends down and starts giving Dean head. He slowly starts with the tip licking the slit and taking him in down to his shaft. He starts going faster and Dean Moans in delightful pleasure. He knows that he is about to Cum but he also knows that if he does he will be punished.

"Ca..C...Cas...Please can i" Dean barely gets those words out

"OK you may" Cas smirks again.

Cas starts Stroking Deans cock even faster and it doesn't take long before he Cums all over himself.


	3. Chapter 3

Deans head fell forward his legs quivering Cas chuckled still holding Deans now flaccid cock. Dean opened his eyes staring at the pool of cum on the floor below him. He was too exhausted to lift his head to see why Cas was chuckling.

"Wow Dean, you really couldn't hold it back. Look at this mess" He said Sarcastically,

Dean was waiting for Cas to let him down from his chains and allow him to go to his room but then he remembered that he had a plug up his ass. He almost forgot about it.

"Well onto phase two," Cas said walking around towards Deans back chuckling at himself as he does so. He firmly gripped Deans ass and spread his cheeks apart and aggressively yanked out the butt plug.

Dean yelled" What the Fuck Cas?"

He soon realized his mistake because the room became dead silent. Dean couldn't help it, it was just so sudden and shocking that was the first thing that popped into deans head. He knew he was going to be punished.

"What Did You Fucking Say To Me," Cas snapped.

Dean didn't know if he should answer the question or not. Cas walked around to face Dean and yanked his face up to his. Now Dean knew he was in trouble, He saw Cas's eyes and they were filled with Lustful anger and power.

"Well, we know what happens when we disobey orders right?" Cas lifted an eyebrow and smirked.

Cas walked over to a wall of whips and picked up a big one with seven heads. Dean started to panic as Cas walked up behind him * **SMACK*** one...two...three... Blood started dripping down Deans back, Cas dropped the whip and licked the wounds which made Dean flinch and noticed he had started to become erect as soon as Cas's tongue touched the flesh wounds on Deans back.

"Now, Lets get on to phase two shall we" Cas said whispering in Deans ear.

Cas then grabbed Deans ass firmly and hard and spread his ass cheeks with his hands and then started teasing Deans hole with his fingers, Dean was fully erect at this time and the moment he was waiting for was going to happen was going to happen. Cas then stuck two of his fingers into Dean as Cas started to unbuckle his pants. Cas took his finger out of Dean and started rubbing his Cock against Dean. Dean moaned in pleasure and it seemed to be OK with Cas because Cas didn't stop what he was doing. Cas then started teasing his hole which made Dean start dripping some precum onto the floor which made Cas chuckle. Cas's Tip was going in just a bit into Dean enough to make Dean scream internally.

"Just do it" Dean internally begged Cas. "Please"

Cas then without hesitation rammed his cock straight into Dean. Dean let out a painfully pleasurable moan and Cas smiled and cocked his head as he continued to fuck Dean wildly. Faster and faster Cas went, Dean angled himself so that Cas could get to his spot, Cas was ramming into Dean without missing a beat in a motion he finally hit Deans spot and Dean moaned with absolute ectacy he was about to cum, He wanted to cum

"Don't Cum" Cas whispered into Deans ear as he grabbed Deans cock.

Cas was hitting Deans spot so many times he didn't know if he could hold himself anymore or even talk himself out of it like last time.

Cas sped up a few more times before filling Deans ass full of hot cum, so much that it drips onto the floor. Cas still thrusting starts stroking Deans cock.

"Good boy Dean" Cas says pulling out of Dean.

Cas continues stroking Deans cock till he cums all over Cas's hands. He walks over to get a towel and grabs one and cleans himself off.

"You're free now" Cas says turning away from him.

Dean walks out of the room and up the stairs. Still naked he walks into his room and into the shower, the thoughts running through his mind were coming at him a mile a minute. He washed the old dried blood off him but could not stop thinking about the touch of Cas on his skin.


End file.
